#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022743.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022743
loop_
_publ_author_name
'Gary A. Molander'
'Barbara Czakó'
'Michael Rheam'
_publ_section_title
;
 Construction of Bicyclic Ring Systems via a Transannular
 SmI₂-Mediated Ketone-Olefin Cyclization Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1755
_journal_page_last               1764
_journal_paper_doi               10.1021/jo062292d
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C11 H20 O'
_chemical_formula_weight         168.27
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      82
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.694(2)
_cell_length_b                   15.694(2)
_cell_length_c                   8.2592(12)
_cell_measurement_temperature    143(1)
_cell_volume                     2034.2(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8331
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4739
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_coef       0.000(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.401
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.401
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.1060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3133
_refine_ls_wR_factor_ref         0.3359
_reflns_number_gt                1472
_reflns_number_total             1785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062292dsi20061107_122938.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'I -4 '
_cod_database_code               4022743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.61682(16) 0.96159(16) 0.2786(5) 0.0690(10) Uani 1 1 d .
H1 H 0.6279 0.9553 0.1823 0.103 Uiso 1 1 calc R
C1 C 0.6776(2) 0.9141(2) 0.3755(5) 0.0593(11) Uani 1 1 d .
C2 C 0.7001(3) 0.8324(3) 0.2820(6) 0.0684(12) Uani 1 1 d .
H2A H 0.7511 0.8091 0.3312 0.091 Uiso 1 1 calc R
H2B H 0.6546 0.7919 0.3019 0.091 Uiso 1 1 calc R
C3 C 0.7147(3) 0.8344(4) 0.1039(7) 0.0813(14) Uani 1 1 d .
H3A H 0.6708 0.8699 0.0561 0.108 Uiso 1 1 calc R
H3B H 0.7063 0.7771 0.0629 0.108 Uiso 1 1 calc R
C4 C 0.8003(4) 0.8659(4) 0.0424(8) 0.0944(18) Uani 1 1 d .
H4A H 0.8457 0.8370 0.1001 0.125 Uiso 1 1 calc R
H4B H 0.8058 0.8523 -0.0717 0.125 Uiso 1 1 calc R
C5 C 0.8089(4) 0.9599(3) 0.0654(7) 0.0801(14) Uani 1 1 d .
H5A H 0.7531 0.9843 0.0850 0.107 Uiso 1 1 calc R
H5B H 0.8313 0.9851 -0.0331 0.107 Uiso 1 1 calc R
C6 C 0.8730(4) 0.9843(4) 0.2193(12) 0.118(3) Uani 1 1 d .
H6A H 0.9286 0.9597 0.1987 0.157 Uiso 1 1 calc R
H6B H 0.8799 1.0457 0.2227 0.157 Uiso 1 1 calc R
C7 C 0.8415(3) 0.9535(3) 0.3882(11) 0.103(2) Uani 1 1 d .
H7A H 0.8470 0.8920 0.3942 0.137 Uiso 1 1 calc R
H7B H 0.8775 0.9780 0.4715 0.137 Uiso 1 1 calc R
C8 C 0.7492(3) 0.9780(3) 0.4215(6) 0.0630(11) Uani 1 1 d .
H8 H 0.7376 1.0320 0.3664 0.084 Uiso 1 1 calc R
C9 C 0.7376(7) 0.9921(6) 0.6058(8) 0.129(3) Uani 1 1 d .
H9A H 0.7773 0.9571 0.6665 0.171 Uiso 1 1 calc R
H9B H 0.7472 1.0514 0.6336 0.171 Uiso 1 1 calc R
C10 C 0.6445(5) 0.9660(4) 0.6435(8) 0.103(2) Uani 1 1 d .
H10A H 0.6370 0.9518 0.7569 0.137 Uiso 1 1 calc R
H10B H 0.6045 1.0103 0.6133 0.137 Uiso 1 1 calc R
C11 C 0.6363(4) 0.8886(3) 0.5365(7) 0.0793(15) Uani 1 1 d .
H11A H 0.5769 0.8739 0.5208 0.106 Uiso 1 1 calc R
H11B H 0.6656 0.8403 0.5839 0.106 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0477(14) 0.0478(14) 0.111(3) 0.0063(14) -0.0057(14) 0.0061(12)
C1 0.0494(18) 0.0540(19) 0.075(3) -0.0033(18) -0.0053(17) 0.0041(15)
C2 0.065(2) 0.061(2) 0.079(3) 0.000(2) -0.004(2) 0.013(2)
C3 0.084(3) 0.083(3) 0.077(3) -0.010(2) 0.011(2) 0.005(3)
C4 0.105(4) 0.082(3) 0.096(4) -0.012(3) 0.029(3) -0.011(3)
C5 0.089(3) 0.070(3) 0.081(3) 0.003(2) 0.010(3) -0.001(3)
C6 0.084(3) 0.070(3) 0.200(9) -0.004(4) 0.060(5) -0.018(3)
C7 0.055(2) 0.063(3) 0.192(8) 0.016(4) -0.022(3) -0.011(2)
C8 0.057(2) 0.056(2) 0.075(3) -0.0011(17) -0.0060(19) -0.0134(17)
C9 0.190(8) 0.130(5) 0.066(3) -0.018(3) 0.016(4) -0.087(6)
C10 0.127(5) 0.093(4) 0.089(4) -0.022(3) 0.042(4) -0.027(4)
C11 0.088(3) 0.071(3) 0.079(3) -0.007(2) 0.016(2) -0.021(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C11 109.5(4)
O1 C1 C2 107.6(3)
C11 C1 C2 108.3(4)
O1 C1 C8 106.2(3)
C11 C1 C8 105.2(4)
C2 C1 C8 119.7(3)
C3 C2 C1 120.9(4)
C2 C3 C4 118.3(5)
C5 C4 C3 111.0(5)
C4 C5 C6 112.3(5)
C7 C6 C5 114.9(4)
C8 C7 C6 112.6(5)
C7 C8 C9 108.9(6)
C7 C8 C1 118.7(4)
C9 C8 C1 104.4(4)
C10 C9 C8 105.7(6)
C11 C10 C9 100.1(5)
C10 C11 C1 105.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.451(5)
C1 C11 1.533(7)
C1 C2 1.538(5)
C1 C8 1.552(5)
C2 C3 1.489(8)
C3 C4 1.518(8)
C4 C5 1.495(8)
C5 C6 1.665(12)
C6 C7 1.558(12)
C7 C8 1.524(7)
C8 C9 1.549(7)
C9 C10 1.549(11)
C10 C11 1.507(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8256317
